EPISODE · Sep 15, 2025 · 2H 8M

Timothy Olyphant

Timothy Olyphant (Alien: Earth, Deadwood, Once Upon a Time in Hollywood) is an Emmy Award-nominated actor. Timothy joins the Armchair Expert to discuss whether he gives middle child vibes, the benefits of being a skills generalist, and why his smile always designated him as the “talk-to-the-cops guy.” Timothy and Dax talk about how knocking things off balance a little bit can create a lovely vulnerable moment, invoking Lou Reed and Bob Dylan as interview inspiration, and being the favorite co-star of so many talented actors. Timothy explains that there’s a judo to rejecting someone while giving them something, asking the small questions like what is humanity and is it worth saving in Alien: Earth, and finding a space where you help others by doing the thing you do.Follow Armchair Expert on the Wondery App or wherever you get your podcasts. Watch new content on YouTube or listen to Armchair Expert early and ad-free by joining Wondery+ in the Wondery App, Apple Podcasts, or Spotify. Start your free trial by visiting wondery.com/links/armchair-expert-with-dax-shepard/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What this episode covers

Timothy Olyphant (Alien: Earth, Deadwood, Once Upon a Time in Hollywood) is an Emmy Award-nominated actor. Timothy joins the Armchair Expert to discuss whether he gives middle child vibes, the benefits of being a skills generalist, and why his smile always designated him as the “talk-to-the-cops guy.” Timothy and Dax talk about how knocking things off balance a little bit can create a lovely vulnerable moment, invoking Lou Reed and Bob Dylan as interview inspiration, and being the favorite co-star of so many talented actors. Timothy explains that there’s a judo to rejecting someone while giving them something, asking the small questions like what is humanity and is it worth saving in Alien: Earth, and finding a space where you help others by doing the thing you do. Follow Armchair Expert on the Wondery App or wherever you get your podcasts. Watch new content on YouTube or listen to Armchair Expert early and ad-free by joining Wondery+ in the Wondery App, Apple Podcasts, or Spotify. Start your free trial by visiting wondery.com/links/armchair-expert-with-dax-shepard/ now. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Timothy Olyphant

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This episode is 2 hours and 8 minutes long.

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This episode was published on September 15, 2025.

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